WO1990014071A2 - Cosmetic preparations - Google Patents

Cosmetic preparations Download PDF

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Publication number
WO1990014071A2
WO1990014071A2 PCT/EP1990/000783 EP9000783W WO9014071A2 WO 1990014071 A2 WO1990014071 A2 WO 1990014071A2 EP 9000783 W EP9000783 W EP 9000783W WO 9014071 A2 WO9014071 A2 WO 9014071A2
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WO
WIPO (PCT)
Prior art keywords
chitosan
cosmetic preparations
preparations
contain
fungi
Prior art date
Application number
PCT/EP1990/000783
Other languages
German (de)
French (fr)
Other versions
WO1990014071A3 (en
Inventor
Willem Wielinga
Ashley R. Cox
David Lewis
Original Assignee
Rhone-Poulenc Chemicals Limited
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Publication of WO1990014071A2 publication Critical patent/WO1990014071A2/en
Publication of WO1990014071A3 publication Critical patent/WO1990014071A3/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/736—Chitin; Chitosan; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • Numerous cosmetic preparations in particular for skin and hair care, take advantage of the excellent film-forming and / or structure-improving properties of a product obtained from natural chitin, chitosan and various of its derivatives.
  • Chitin a well-known nitrogenous polysaccharide, whose formula indicates its close relationship with cellulose, is an exceptionally resistant material that can only be digested under extreme conditions and practically not completely dissolved. This material forms the main component of the shell of shellfish, such as crabs, insects, lobsters, etc., from which the commercially available chitin and the fully and partially acetylated chitosan obtained from it are produced.
  • chitin is also found in the cell walls of certain bacteria, microorganisms such as algae,
  • Chitosan of excellent quality can be made from the residues of large-scale microbiological production of, for example, citric acid, using microorganisms, in particular so-called fungi imperfecti, such as
  • Mucor cereinelloides also known as Mucor j avanicus
  • u. a. win During these fermen Residue residues have previously caused major problems for disposal and could only be burned, the conversion to chitosan and its use in cosmetics offers a welcome alternative solution.
  • the object of the present invention was therefore to develop new uses for a chitosan which is obtained from microorganisms such as algae, yeast, mold, fungi, bacteria and lichens.
  • This object is, as defined in claim 1, solved by the use of such a chitosan in cosmetic preparations. It should be noted here that the film-forming and / or structure-improving properties of such a cosmetic preparation are significantly improved compared to similar preparations with chitin additives of animal origin, without any disadvantages being able to be demonstrated to date.
  • microalgae of any kind are suitable, molds,
  • the chitosan obtained from such sources is particularly suitable as an additive to skin and hair care products, such as skin creams, lotions, ointments, etc., Sunscreen preparations, hair washing, conditioning and setting agents of known type and composition. Since the chitosan of the origin mentioned has better film-forming and structure-imparting properties than the chitoson of animal origin, often less are sufficient
  • Chitosan F obtained from Apsergillus niger by known methods (boiling with strong sodium hydroxide solution or potassium hydroxide solution for several hours) was dispersed in water and the citric acid was added. After warming slightly, a clear solution was obtained. After cooling, a mixture of the polysorbate with the perfume was added. Finally, the ethanol is added to this mixture and the mixture is filled into spray cans and pressurized with the propellant gas. As a comparison, the same mixture was used using animal chitosan (commercial product obtained from crayfish dishes, here Called "Chitosan C").
  • the product had a pH of 3.2. It was prepared in the usual way by mixing the components at 80 ° C. and cooling with stirring.
  • the chitosan is dissolved in the water-acid mixture and the pH is adjusted to 5.5 with sodium hydroxide solution, whereupon the remaining constituents are stirred in.
  • the chitosan is dissolved in the water-acid mixture. Ceteraeth 25 is added to this solution and stirred until dissolved. After adding PEG-40 hydrogenated castor oil and ethanol, the pH is adjusted to 4.0 and the water is added. The mixture is in
  • Spray cans filled and pressurized with propellant

Abstract

Cosmetic preparations with excellent film-forming or texture-forming properties contain, in addition to the usual components, a chitosan additive obtained from sources other than crustaceans and insects, for example from algae, fungi, yeasts, moulds and lichens. A particularly useful product is obtained by known processes from the culture residues of Fungi imperfecti, such as Aspergillus niger or Mucor cercinelloides, which are produced as waste products of biochemical reactions.

Description

Kosmetische Präparate  Cosmetic preparations
Zahlreiche kosmetische Präparate, insbesondere zur Haut- und Haarpflege, machen sich die ausgezeichneten filmbildenden und/oder strukturverbessernden Eigenschaften eines, aus natürlichem Chitin gewonnenen Produktes, des Chitosans und verschiedener seiner Derivate zu Nutzen. Numerous cosmetic preparations, in particular for skin and hair care, take advantage of the excellent film-forming and / or structure-improving properties of a product obtained from natural chitin, chitosan and various of its derivatives.
Chitin, ein bekanntes stickstoffhaltiges Polysaccharid, dessen Formel auf seine nahe Verwandtschaft mit Cellulose hinweist, ist ein aussergewδhnlich widerstandsfähiges Material, das nur unter extremen Bedingungen aufgeschlossen und praktisch nicht vollständig aufgelöst werden kann. Dieses Material bildet den Hauptbestandteil der Panzer von Schalentieren, wie Krebsen, Insekten, Hummern, usw., aus welchen das handelsübliche Chitin und das daraus erhältliche, voll- und teilentacetylierte Chitosan hergestellt werden.  Chitin, a well-known nitrogenous polysaccharide, whose formula indicates its close relationship with cellulose, is an exceptionally resistant material that can only be digested under extreme conditions and practically not completely dissolved. This material forms the main component of the shell of shellfish, such as crabs, insects, lobsters, etc., from which the commercially available chitin and the fully and partially acetylated chitosan obtained from it are produced.
Chitin findet sich jedoch auch in den Zellwänden gewisser Bakterien, Mirkoorganismen, wie Algen,  However, chitin is also found in the cell walls of certain bacteria, microorganisms such as algae,
Hefen, Pilzen und Flechten. Erstaunlicherweise hat sich herausgestellt , dass ein aus solchen Materialien nach be kannten Methoden isoliertes Chitin nach seiner Entacetylierung zu einem Chitosan-Produkt führt , das sich für Kosmetika , wie Haut - und Haarpflegemitteln , wesentlich besser eignet als die handelsüblichen , aus Schalentieren gewonnenen Produkte . Es sind gegenwärtig Untersuchungen im Gange , um festzustellen , ob sich dieses Phänomen durch Abweichungen der chemischen Struktur oder durch den Einschluss verschiedenartiger Verunreinigungen erklären lässt oder ob es anderen Gründen zuzuschreiben ist . Die bisherigen Untersuchungen haben auf j eden Fall merkliche Abweichungen im Verlauf der IR-Absorptionskurven zwischen derjenigen von Chitosan aus Krebsen und derj enigen von Chitosan aus Hefe- bzw. Schimmelpilzen ergeben . Diese Resultate werden gegenwärtig ausgewertet . Yeast, mushrooms and lichens. Amazingly, has emphasized that a chitin isolated from such materials by known methods after its deacetylation leads to a chitosan product which is much better suited for cosmetics such as skin and hair care products than the commercial products obtained from shellfish. Studies are currently underway to determine whether this phenomenon can be explained by variations in chemical structure or by the inclusion of various types of impurities, or whether it can be attributed to other reasons. In any case, the previous investigations have shown noticeable deviations in the course of the IR absorption curves between that of chitosan from crabs and that of chitosan from yeasts and molds. These results are currently being evaluated.
Die Gewinnung von Chitosan aus den oben genannten mikrobiologischen Ausgangsmaterialien , welche Gewinnung zum Stand der Technik gehört und nicht Gegenstand der vorliegenden Erfindung ist , bietet nicht übersehbare Vorteile inbezug auf Naturschutz und Entsorgung . Chitosan ausgezeichneter Qualität lässt s ich aus den Rückständen der grosstechnischen mikrobiologischen Herstellung von zum Beispiel Zitronensäure , unter Einsatz von Mirkoorganismen , insbesondere sogenannte Fungi imperfecti , wie  The extraction of chitosan from the above-mentioned microbiological starting materials, which extraction belongs to the state of the art and is not the subject of the present invention, offers obvious advantages with regard to nature conservation and disposal. Chitosan of excellent quality can be made from the residues of large-scale microbiological production of, for example, citric acid, using microorganisms, in particular so-called fungi imperfecti, such as
Aspergillus nige r , Mucor cereinelloides (auch bekannt als Mucor j avanicus) u. a . gewinnen . Während diese Fermen tationsrückstände bisher grosse Probleme für die Entsorgung nach sich zogen und nur verbrannt werden konnten, bietet die Umarbeitung zu Chitosan udn dessen Einsatz in der Kosmetik eine willkommene Alternativlösung. Aspergillus nige r, Mucor cereinelloides (also known as Mucor j avanicus) u. a. win . During these fermen Residue residues have previously caused major problems for disposal and could only be burned, the conversion to chitosan and its use in cosmetics offers a welcome alternative solution.
Aufgabe der vorliegenden Erfindung war es daher, neue Verwendungsmöglichkeiten für ein Chitosan zu entwickeln, das aus Mikroorganismen, wie Algen, Hefen, Schimmel, Pilzen, Bakterien und Flechten gewonnen wird. Diese Aufgabe wird, wie in Patentanspruch 1 definiert, durch den Einsatz eines solchen Chitosans in kosmetischen Präparaten gelöst. Hierbei ist zu beachten, dass die filmbildenden und/oder strukturverbessernden Eigenschaften eines solchen kosmetischen Präparates gegenüber ähnlichen Präparaten mit chitinadditiven tierischen Ursprungs wesentlich verbessert sind, ohne dass bisher irgendwelche Nachteile nachgewiesen werden konnten.  The object of the present invention was therefore to develop new uses for a chitosan which is obtained from microorganisms such as algae, yeast, mold, fungi, bacteria and lichens. This object is, as defined in claim 1, solved by the use of such a chitosan in cosmetic preparations. It should be noted here that the film-forming and / or structure-improving properties of such a cosmetic preparation are significantly improved compared to similar preparations with chitin additives of animal origin, without any disadvantages being able to be demonstrated to date.
Als Ausgangsmaterial für das in den erfindungs- gemässen kosmetischen Präparaten verwendete Chitosan  As the starting material for the chitosan used in the cosmetic preparations according to the invention
eignen sich Mikroalgen jeglicher Art, Schimmelpilze, microalgae of any kind are suitable, molds,
Hefen und viele andere Mikroorganismen, insbesondere Yeast and many other microorganisms, in particular
solche, die bei industriellen Herstellungsverfahren in grossen Mengen eingesetzt werden und nach erfolgter Reaktion als Abfallprodukt anfallen. Those that are used in large quantities in industrial production processes and are produced as waste products after the reaction.
Das aus solchen Quellen erhaltene Chitosan ist besonders geeignet als Zusatz zu Haut- und Haarpflegemitteln, wie Hautcremen, -lotionen, -salben, usw., Sonnenschutzpräparaten, Haarwasch-, -konditionier- und -festigungsmitteln bekannter Art und Zusammensetzung. Da das Chitosan der genannten Herkunft bessere filmbildende und strukturverleihende Eigenschaften aufweist als das Chitoson tierischer Herkunft, genügen oft geringere The chitosan obtained from such sources is particularly suitable as an additive to skin and hair care products, such as skin creams, lotions, ointments, etc., Sunscreen preparations, hair washing, conditioning and setting agents of known type and composition. Since the chitosan of the origin mentioned has better film-forming and structure-imparting properties than the chitoson of animal origin, often less are sufficient
Mengen, um dieselbe Wirkung, zu erzielen. Amounts to achieve the same effect.
Beispiel 1  example 1
Haar-styling-Schaum  Hair styling foam
Chitosan F 1 , 0 G ew. -% Chitosan F 1.0 wt% -%
Polysorbat 20 3 , 0 "Polysorbate 20 3.0 "
Aethanol 8 , 0 "Ethanol 8.0 "
Zitronensäure (50 %) 3 , 0 "Citric acid (50%) 3.0 "
Parfüm 0, 1 "Perfume 0.1 "
Wasser 76 , 9 "Water 76, 9 "
Treibgas 8 , 0 " Propellant gas 8.0 "
Chitosan F, erhalten aus Apsergillus niger nach bekannten Verfahren (Kochen mit starker Natronlauge oder Kalilauge während mehreren Stunden) wurde in Wasser dispergiert und mit der Zitronensäure versetzt. Nach schwachem Erwärmen entstand eine klare Lösung. Nach dem Erkalten wurde ein Gemisch des Polysorbates mit dem Parfüm zugesetzt. Diesem Gemisch wird schliesslich das Aethanol beigegeben und das Gemisch in Sprühdosen abgefüllt und mit dem Treibgas unter Druck gesetzt. Als Vergleich wurde dieselbe Mischung unter Verwendung von tierischem Chitosan (aus Krebsschalen erhaltenes Handelsprodukt, hier "Chitosan C" genannt) hergestellt. Chitosan F, obtained from Apsergillus niger by known methods (boiling with strong sodium hydroxide solution or potassium hydroxide solution for several hours) was dispersed in water and the citric acid was added. After warming slightly, a clear solution was obtained. After cooling, a mixture of the polysorbate with the perfume was added. Finally, the ethanol is added to this mixture and the mixture is filled into spray cans and pressurized with the propellant gas. As a comparison, the same mixture was used using animal chitosan (commercial product obtained from crayfish dishes, here Called "Chitosan C").
Beide Produkte wurden auf übliche Weise inbezug auf ihre fixierende Wirkung auf je sechs Proben ä 2 g derselben Haarlocken von 17 cm Länge getestet, welche mit je 0,1 g des einen oder anderen Schaumes behandelt und bei 25ºC und 90 % relativer Feuchtigkeit während verschiedenen Zeiten gelagert wurden.  Both products were tested in the usual way with regard to their fixing effect on six samples of 2 g of the same locks of hair of 17 cm length, which were treated with 0.1 g of one or the other foam and at 25 ° C. and 90% relative humidity for different times were stored.
Die Resultate waren die folgenden :  The results were as follows:
Figure imgf000007_0001
Figure imgf000007_0001
Beispiel 2 Example 2
Feuchtigkeitslotion  Moisturizing lotion
Mineralöl 15,0 Gew.-% Mineral oil 15.0% by weight
Cetylalkohol 2,0 " Cetyl alcohol 2.0 "
Glycerylstearat )  Glyceryl stearate)
PEG 100 -Stearat) 10,0 "  PEG 100 stearate) 10.0 "
Chitosan F 0,6 "  Chitosan F 0.6 "
Zitronensäure (50 %) 1,6 "  Citric acid (50%) 1.6 "
destilliertes Wasser ad 100,0 " Das Produkt wies ein pH von 3,2 auf. Seine Herstellung erfolgte auf übliche Weise durch Vermischen der Bestandteile bei 80°C und Abkühlen unter Rühren. distilled water ad 100.0 " The product had a pH of 3.2. It was prepared in the usual way by mixing the components at 80 ° C. and cooling with stirring.
Beispiel 3  Example 3
Konditicnierungsshampoo  Conditioning shampoo
Natrium-laureth-sulfat (24 %) 10,0 Gew.-% Sodium laureth sulfate (24%) 10.0% by weight
Cocamidopropylbetain (35 %) 30,0 "Cocamidopropyl betaine (35%) 30.0 "
Polysorbat 20 0,5 "Polysorbate 20 0.5 "
Chitosan F 0,5 "Chitosan F 0.5 "
Salzsäure (37 %) 0.5 " Hydrochloric acid (37%) 0.5 "
Duftstoffe und Konservierungsmittel q.s. Fragrances and preservatives q.s.
Wasser ad 100,0 " pH : 6,5  Water ad 100.0 "pH: 6.5
Das Chitosan wird in der Wasser-Säure-Mischung gelöst und das pH mit Natriumhydroxydlösung auf 5 , 5 eingestellt , worauf die übrigen Bestandteile eingerührt werden,  The chitosan is dissolved in the water-acid mixture and the pH is adjusted to 5.5 with sodium hydroxide solution, whereupon the remaining constituents are stirred in.
Beispiel 4  Example 4
Haarspfllung  Hair conditioner
Chitosan F 2,0 Gew.-% Chitosan F 2.0% by weight
Hydroxypropyl-guar 0,75 " Hydroxypropyl guar 0.75 "
Salzsäure (37 %) 1,5 "  Hydrochloric acid (37%) 1.5 "
Polysorbat 20 3,0 "  Polysorbate 20 3.0 "
Propylenglykol 20,0 "  Propylene glycol 20.0 "
Duftstoffe und Konservierungsmittel q.s.  Fragrances and preservatives q.s.
Wasser ad 100,0 " pH : 4,5 Das Chitosan wird in der Wasser-Säure-Mischung gelöst. Das Hydroxypropyl -guar wird in der Lösung dispergiert und bis zur völligen Lösung, gerührt. Anschliessend werden die übrigen Bestandteile zugemischt und das pH mit NaOH-Lösung auf 4,5 eingestellt. Water ad 100.0 "pH: 4.5 The chitosan is dissolved in the water-acid mixture. The hydroxypropyl guar is dispersed in the solution and stirred until completely dissolved. The remaining constituents are then mixed in and the pH is adjusted to 4.5 using NaOH solution.
Beispiel 5  Example 5
Haarfestiger-Schaum  Hair setting foam
Chitosan F 2 , 2 Gew. - % Chitosan F 2, 2 wt.%
Ceteraeth 25 0 , 1 II Ceteraeth 25 0, 1 II
PEG-40 hydriertes Rhizinusδl 0 , 3 II PEG-40 hydrogenated castor oil 0.3 III
Salzsäure (37 %) 1 , 5 II Hydrochloric acid (37%) 1, 5 II
Aethanol 8 , 0 II Ethanol 8.0 II
NaOH zur Einstellung des NaOH to adjust the
pH auf 4,0  pH to 4.0
Wasser ad 92,0  Water ad 92.0
Treibgas 8,0 II  Propellant 8.0 II
Das Chitosan wird im Wasser-Säure-Gemisch gelöst. Dieser Lösung wird das Ceteraeth 25 zugesetzt und bis zur Auflösung gerührt. Nach Zusatz von PEG-40 hydriertem Rhizinusöl und Aethanol wird der pH auf 4,0 eingestellt und das Wasser zugesetzt. Das Gemisch wird in The chitosan is dissolved in the water-acid mixture. Ceteraeth 25 is added to this solution and stirred until dissolved. After adding PEG-40 hydrogenated castor oil and ethanol, the pH is adjusted to 4.0 and the water is added. The mixture is in
Sprühdosen eingefüllt und mit Treibgas unter Druck gesetzt. Spray cans filled and pressurized with propellant.
Beispiel 6  Example 6
Die filmbildenden Eigenschaften von Chitosan F und Chitosan C wurden verglichen. Von beiden Substanzen wurden 1 *ige Lösungen in destilliertem Wasser , das mit Zitronensäure auf pH 3 , 3 eingestellt war , hergestellt . Beide Chitosane ergaben klare , nicht-viskose Lösungen . The film-forming properties of Chitosan F and Chitosan C were compared. 1 * solutions of both substances were prepared in distilled water, which was adjusted to pH 3.3 with citric acid. Both chitosans gave clear, non-viscous solutions.
Je 2 ml der beiden Lösungen wurden über die Oberfläche von gereinigten Glasplatten (20 x 5 cm) verteilt und trocknen gelassen . Das Trocknen wurde vervollständigt in einem Luftofen bei 60ºC während 10 Minuten, und die erhaltenen Filme wurden sodann bei 25°C und 65 % relativer Feuchtigkeit während 18 Stunden konditioniert.  2 ml each of the two solutions were distributed over the surface of cleaned glass plates (20 × 5 cm) and left to dry. Drying was completed in an air oven at 60 ° C for 10 minutes and the resulting films were then conditioned at 25 ° C and 65% relative humidity for 18 hours.
Die erhaltenen Filme wurden sodann bezüglich Klarheit , Farbe , Glanz , Gefühl , Härte und Biegsamkeit begutachtet . Beide Chitosane ergaben klare , farblose, glänzende , trockene Filme von annehmbarer Härte . Die Chitosan-C-Filme bildeten jedoch beim Ritzen mit einer Messerspitze sofort Risse , während der biegsame Chitosan- F-Film bei derselben Behandlung unversehrt blieb .  The films obtained were then assessed for clarity, color, gloss, feel, hardness and flexibility. Both chitosans gave clear, colorless, glossy, dry films of acceptable hardness. However, the chitosan-C films immediately cracked when scribed with a knife tip, while the flexible chitosan-F film remained intact with the same treatment.

Claims

P a t e n t a n s p r ü c h e Patent claims
1. Kosmetische Präparate, insbesondere Haut- und Haarpflegemittel, dadurch gekennzeichnet, dass sie Chitosan mikrobiologischen Ursprungs als Zusatz enthalten, 1. Cosmetic preparations, in particular skin and hair care products, characterized in that they contain chitosan of microbiological origin as an additive,
2. Präparate nach Patentanspruch 1, dadurch gekennzeichnet, dass sie Chitosan enthalten, das aus  2. Preparations according to claim 1, characterized in that they contain chitosan from
Bakterien, Algen, Pilzen, Hefen, Schimmel oder Flechten erhalten wurde. Bacteria, algae, fungi, yeast, mold or lichens have been preserved.
3. Präparate nach Patentanspruch 2, dadurch gekennzeichnet, dass sie Chitosan enthalten, das aus dem Rückstand einer Mikroorganismenkultur erhalten wurde.  3. Preparations according to claim 2, characterized in that they contain chitosan, which was obtained from the residue of a microorganism culture.
4. Präparate nach Patentanspruch 3, dadurch gekennzeichnet, dass sie Chitosan enthalten, das aus dem Rückstand einer Kultur von Aspergillus niger erhalten wurde.  4. Preparations according to claim 3, characterized in that they contain chitosan, which was obtained from the residue of a culture of Aspergillus niger.
5. Präparate nach Patentanspruch 3, dadurch gekennzeichnet, dass sie Chitosan enthalten, das aus dem Rückstand von Mucor cercinelloides erhalten wurde.  5. Preparations according to claim 3, characterized in that they contain chitosan, which was obtained from the residue of Mucor cercinelloides.
6. Chitosan, gewonnen aus mikrobiologischem Material.  6. Chitosan, made from microbiological material.
7. Chitosan F, gewonnen aus Aspergillus niger, gekennzeichnet durch ein JR-Absorptionsspektrum gemäss Figur 2. 7. Chitosan F, obtained from Aspergillus niger, characterized by a JR absorption spectrum according to FIG. 2.
8. Chitosan F, gewonnen aus Mucor javanicus, gekennzeichnet durch ein IR-Absorptionsspektrum gemäss Figur 3. 8. Chitosan F, obtained from Mucor javanicus, characterized by an IR absorption spectrum according to FIG. 3.
PCT/EP1990/000783 1989-05-17 1990-05-15 Cosmetic preparations WO1990014071A2 (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0403282A2 (en) * 1989-06-15 1990-12-19 Unilever Plc Hair setting composition
EP0531991A2 (en) * 1991-09-11 1993-03-17 Shin-Etsu Chemical Co., Ltd. Method for preparing chitosan
WO1996025437A1 (en) * 1995-02-13 1996-08-22 Abion Beteiligungs- Und Verwaltungsgesellschaft Mbh Process for producing chitosan-glucan complexes, compounds producible therefrom and their use
WO2001043713A2 (en) * 1999-12-16 2001-06-21 Cognis Deutschland Gmbh & Co.Kg Cosmetic agent containing natural chitosans

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JPS537471A (en) * 1976-07-06 1978-01-23 Mitsui Toatsu Chemicals Soil conditioner containing microorganisms
JPS59139310A (en) * 1983-01-31 1984-08-10 Shiseido Co Ltd Emulsified composition

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Database WPI / Derwent, AN 78-18287A, & JP, A, 53007471 (Mitsui Toatsu CHem. Inc.) 23. Januar 1978 siehe Zusammenfassung *
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PATENT ABSTRACTS OF JAPAN, Band 8, Nr. 260 (C-254)(1697), 29. November 1984, & JP, A, 59139310 (Shiseido K.K.) 10. August 1984 siehe Zusammenfassung *
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0403282A2 (en) * 1989-06-15 1990-12-19 Unilever Plc Hair setting composition
EP0403282A3 (en) * 1989-06-15 1991-08-21 Unilever Plc Hair setting composition
EP0531991A2 (en) * 1991-09-11 1993-03-17 Shin-Etsu Chemical Co., Ltd. Method for preparing chitosan
EP0531991A3 (en) * 1991-09-11 1994-03-02 Shinetsu Chemical Co
WO1996025437A1 (en) * 1995-02-13 1996-08-22 Abion Beteiligungs- Und Verwaltungsgesellschaft Mbh Process for producing chitosan-glucan complexes, compounds producible therefrom and their use
US6333399B1 (en) 1995-02-13 2001-12-25 Alexander Teslenko Process for producing chitosan-glucan complexes, compounds producible therefrom and their use
WO2001043713A2 (en) * 1999-12-16 2001-06-21 Cognis Deutschland Gmbh & Co.Kg Cosmetic agent containing natural chitosans
DE19960632A1 (en) * 1999-12-16 2001-07-05 Cognis Deutschland Gmbh Cosmetics containing natural chitosans
WO2001043713A3 (en) * 1999-12-16 2002-05-23 Cognis Deutschland Gmbh Cosmetic agent containing natural chitosans

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WO1990014071A3 (en) 1991-01-10

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